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Acta Cryst. (2012). E68, o84  [ doi:10.1107/S1600536811052470 ]

9-[(E)-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-9H-carbazole

Y. Hatayama and T. Okuno

Abstract: The title compound, C20H22BNO2, is a simple olefinic compound which carries both B and N atoms that are trans to one another. The [pi]-conjugated system of the compound is considered to be isoelectronic with 1,3-butadiene. There are two independent molecules in the asymmetric unit in which the environments around the boron atoms are essentially planar (r.m.s. deviations of 0.0032 and 0.0021 Å for the BO2C planes). The dihedral angles of the olefinic planes with the boron planes are 5.70 (11) and 9.74 (9)°, respectively, while the dihedral angles of the olefinic planes with the carbazole planes are 19.37 (3) and 10.74 (6)°. These dihedral angles are consistent with those in 9-ethenylcarbazole and an ethenylboronic ester derivative. The N-Csp2, B-Csp2 and C=C bond lengths suggest that the contribution of the canonical structure can be described as N+=C-C=B-.

Online 10 December 2011


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